CHEBI:17710 - (R)-mevalonic acid

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ChEBI Name (R)-mevalonic acid
ChEBI ID CHEBI:17710
ChEBI ASCII Name (R)-mevalonic acid
Definition The (R)-enantiomer of mevalonic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:345, CHEBI:18691
Supplier Information ChemicalBook:CB8325514, eMolecules:29541141, eMolecules:496898, eMolecules:29549277, ZINC000003914810
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Inosinic acid or inosine monophosphate (IMP) is a nucleotide (that is, a nucleoside monophosphate). Widely used as a flavor enhancer, it is typically obtained from chicken byproducts or other meat industry waste. Inosinic acid is important in metabolism. It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides. It can also be formed by the deamination of adenosine monophosphate by AMP deaminase. It can be hydrolysed to inosine. The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase, encoded by YJR069C in Saccharomyces cerevisiae and containing (d)ITPase and (d)XTPase activities, hydrolyzes inosine triphosphate (ITP) releasing pyrophosphate and IMP. Important derivatives of inosinic acid include the purine nucleotides found in nucleic acids and adenosine triphosphate, which is used to store chemical energy in muscle and other tissues. In the food industry, inosinic acid and its salts such as disodium inosinate are used as flavor enhancers. It is known as E number reference E630.
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Formula C6H12O4
Net Charge 0
Average Mass 148.15710
Monoisotopic Mass 148.07356
InChI InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
InChIKey KJTLQQUUPVSXIM-ZCFIWIBFSA-N
SMILES C[C@@](O)(CCO)CC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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ChEBI Ontology
Outgoing (R)-mevalonic acid (CHEBI:17710) is a 3,5-dihydroxy-3-methylpentanoic acid (CHEBI:194519)
(R)-mevalonic acid (CHEBI:17710) is conjugate acid of (R)-mevalonate (CHEBI:36464)
(R)-mevalonic acid (CHEBI:17710) is enantiomer of (S)-mevalonic acid (CHEBI:28880)
Incoming (R)-3-phosphomevalonic acid (CHEBI:83564) has functional parent (R)-mevalonic acid (CHEBI:17710)
(R)-5-diphosphomevalonic acid (CHEBI:15899) has functional parent (R)-mevalonic acid (CHEBI:17710)
(R)-5-phosphomevalonic acid (CHEBI:17436) has functional parent (R)-mevalonic acid (CHEBI:17710)
mevalonic acid (CHEBI:25351) has part (R)-mevalonic acid (CHEBI:17710)
(R)-mevalonate (CHEBI:36464) is conjugate base of (R)-mevalonic acid (CHEBI:17710)
(S)-mevalonic acid (CHEBI:28880) is enantiomer of (R)-mevalonic acid (CHEBI:17710)
IUPAC Name
(3R)-3,5-dihydroxy-3-methylpentanoic acid
Synonyms Sources
(−)-mevalonic acid ChEBI
(3R)-3,5-dihydroxy-3-methylvaleric acid ChEBI
(3R)-mevalonic acid ChEBI
(R)-(−)-mevalonic acid ChEBI
(R)-3,5-dihydroxy-3-methylpentanoic acid ChEBI
(R)-3,5-dihydroxy-3-methylvaleric acid ChEBI
D-mevalonic acid ChEBI
R-mevalonic acid ChEBI
R-MVA ChEBI
Manual Xrefs Databases
C00001195 KNApSAcK
C00418 KEGG COMPOUND
DB03518 DrugBank
LMFA01050352 LIPID MAPS
Mevalonic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1722593 Reaxys Registry Number Reaxys
17817-88-8 CAS Registry Number KEGG COMPOUND
Last Modified
23 March 2023